Vat dyes and process of making them.



UETED TATE% PAENT @dh l i ifio OSCAR RALLY, OF MANNHEIM, GERMANY, ASSIGNOR TO BADISCHE ANILIN' & SODA FABRIK, OF LUDWIGSHAFEN-ON-THE-RHINE, GERMANY, A CORPORATION.

VAT DYES AND PROCESS OF MAKING THEM.

No Drawing.

To all whom it may concern:

Be it known that I, Oscan BALLY, Ph. D., chemist, citizen of the Swiss Republic, residing at Mannheim, Germany, have invented new and useful Improvements in Vat Dyes and Processes of Making Them, of which the following is a specification.

In the specification of Patent No. 1,128,836, Serial No. 784,811, I have described a new class of coloring matters which are amino derivatives of dibnzanthrones containing an organic radical in the amino group, and the specification of application for patent Serial No. 804 ,7l% states that the same or similar coloring inatters can be obtained by introducing an aldehyde radical into a leuco compound of an a1ninodibenzanthrone. In neither ot the said applications is a coloring matter containing halogen mentioned or described.

I have now discovered that those deriva tives of amino-dibenzanthrones which contain both an organic radical in the amino group and also halogen in the'molecule are particularly valuable, since they give on cotton shades which are clearer and considerably redder" than the corresponding dyes which are free from halogen. In this application I regard the expression (libcnzanthrone as including those compounds which are regarded as possessing the dibenzanthrone grouping possessing probably the structu 'al formula:

and also those which are regarded as pos- Specification of Letters Patent.

Patented Oct. 2st, 1916.

Application filed October 21, 19 14. Serial No. 867,717.

sessing the iso dilienzanthrone grouping, the

My new compounds may contain halogen either attached to the 'dihenzanthrone nucleus or to the organic radical, or they may contain halogen in both these positions. The introduction of the halogen can. take place either by employing halogenated initial materials, for instance, halogenated amino-. dil)enzanthrones, or halogenated aldehydes, acid chlorids and the like, or the ready formed coloring matter, obtained as described in either of the aforesaid specifications, can he subsequently halogenated.

My new compounds possess the general characteristics ot-the dyes claimed in my previous application Serial No.- 7S l,8l1, that is to say, they consist when dry of .dark powders and yield from blue to blnc violet solutions in concentrated sulfuric acid. 'Ihey dye cotton from a hydrosullitc vat from red to Korcleaux shades and are distinguislndlrom the dyes specifically mcntioned in my said previous application in that tley contain halogen. The Iollowing examples will serve to illustrate further the nature'ot this invention, which, lmwevcr, is not confined to these examples. The parts are by Weight.

Example I: lloil together one part of amino-cila-nzanthronc and ten parts of ortho-chlor-benzaldehyde, whereupon the green color of the melt rapidly turns red. When the shade no longer alters. the reaction is finished and on allowing the mass to cool, the coloring matter crystallizes out.

Filter this off and free it from excesg of ortho-cl1lor-benzaldehyde. It yields a pure blue rat in alkaline hydrosulfite solution and dyes cotton full Bordeaux shades.

Example 2: densation product obtainable according to the foregoing Example 1 in twenty parts of nitrobenzene, all three parts of sulfuryl chlorid and one-tenth of a part of iodin and heat on the water bath until the evolution oi. hydrochloric acid ceases. Then boil for a short tiniegallow the mass to cool and filter oil the coloring matter and wash it with alcohol and then dry it. lt dyes cotton 'froin the hydrosultite vat brilliant red shades of excellent fastness.

Instead of sulfuryl chlorid, other halogenating' agent's canbe employed, either with, or without, the addition of halogen carriers, and, if desired, the nitrobenzene can be replaced by other solvent, or diluent.

Now what I claim is 1. The new vat dyes which are amino derivatives of a dibenzanthrone containing an ore ganic radical attached to the annno group and also contain halogen, which new dyes consist when dry of dark powders, yield froni'blue to blue-violet solutions in concentrated sulfuric acid and dye cotton from uspend one part of the c0n-- a hydrosulfite vat from red to Bordeaux shades 2. The new vat dye which is an aminodibenzanthrone substituted in the amino group by an ortho-chlor-beuzaldehyde residue, which new coloring matter contains chlorin and consists when dry of a dark powder, which yields a violet-blue solution in concentrated sulfuric acid and a pure blue vat in alkaline hydrosulfite solution and dyes cotton full Bordeaux shades.

The process of producing vat dyes of the anthraquinone series which consists in reacting on an amino derivative of a dibenzanthrone with a substance capable of introducing a halogenated organic radical into the said amino group.

47 The process of producing a vatdye of the anthraquinone series by reacting on aniino-dibenzanthrone with ortho-chlor-benzaldehyde. 7

In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.

OSCAR BALLY. Witnesses H. Manna COCI-IRAN, N. ERNST. 

